title: Stereocontrolled total synthesis of amphidinolide X via a silicon-tethered metathesis reaction.
abstract: Two esterifications and an RCM to create the challenging trisubstituted C12-C13 double bond were required in the total synthesis of amphidinolide X (1) reported here. Assembling the three fragments in this order, no RCM occurred or the process yielded mainly isomer Z. However, generating the E double bond first, by a new variant of a Si-tethered metathesis (using Schrock's catalyst), and carrying out the esterification and macrolactonization steps later, 1 was obtained exclusively.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Barcelona, Catalonia, Spain.
authors.forename: Carles
authors.initials: C
authors.lastname: Rodríguez-Escrich
authors.forename: Fèlix
authors.initials: F
authors.lastname: Urpí
authors.forename: Jaume
authors.initials: J
authors.lastname: Vilarrasa
mesh_terms: D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D000097442:Amphidinolides
chemical_list: D007783:Lactones; D018942:Macrolides; D012825:Silicon; C480942:amphidinolide X; D000097442:Amphidinolides